WO2001013175A2 - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- WO2001013175A2 WO2001013175A2 PCT/KR2000/000883 KR0000883W WO0113175A2 WO 2001013175 A2 WO2001013175 A2 WO 2001013175A2 KR 0000883 W KR0000883 W KR 0000883W WO 0113175 A2 WO0113175 A2 WO 0113175A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chemical formula
- compound
- acrylate
- meth
- group
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 57
- 239000000126 substance Substances 0.000 claims abstract description 79
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 239000011347 resin Substances 0.000 claims abstract description 52
- 229920005989 resin Polymers 0.000 claims abstract description 52
- 239000011230 binding agent Substances 0.000 claims abstract description 43
- 238000004132 cross linking Methods 0.000 claims abstract description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000001555 benzenes Chemical class 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 31
- 239000007864 aqueous solution Substances 0.000 abstract description 9
- 230000004304 visual acuity Effects 0.000 abstract description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 abstract 1
- 239000010408 film Substances 0.000 description 19
- 239000010409 thin film Substances 0.000 description 13
- 230000002194 synthesizing effect Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 238000005286 illumination Methods 0.000 description 9
- -1 acryl Chemical group 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- SDSMQJYIBMHORW-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1h-triazine Chemical compound ClC(Cl)(Cl)N1NC(C(Cl)(Cl)Cl)=CC(C(Cl)(Cl)Cl)=N1 SDSMQJYIBMHORW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
Definitions
- the present invention relates to a light-sensitive resin composition capable of being developed by an alkaline aqueous solution, more particularly to a photosensitive resin composition applicable to a color filter and for thin film transistor circuit passivation in the liquid crystal display manufacturing process.
- Alkaline developing type photosensitive resins have been used in dry film resists for printed circuit board fabrication, photoresists for semiconductor circuit fabrication, etc., and their applications such as color filter and various circuit passivation are recently being expanded into semiconductors and flat panel display fields, including liquid crystal displays.
- a photosensitive resin composition capable of being developed by an alkaline aqueous solution generally comprises a) a binder resin which is dissolved or swelled by an alkaline solution; b) a crosslinking compound having at least two ethylenically unsaturated bonds; c) a photopolymerization initiator; and d) a solvent capable of dissolving the above mentioned constituents, in which dyestuff, pigment, or various additives which improve the filming property or adhesive property to the substrate can be contained if necessary.
- a binder resin which is dissolved or swelled by an alkaline aqueous solution generally comprising a structure containing carboxylic acid or a carboxylic acid anhydride or hydroxide group, an amino group, an amide group in the polymer chains, and a novolak based phenol resin, an acryl based resin homopolymer, or an acryl based resin copolymer, is widely used.
- an acryl based binder resin having superior transparency for visible light rays is widely being used when the photosensitive resin composition is used as a color filter and for thin film transistor circuit passivation in the flat panel display fields.
- Copolymers using one or more compounds selected from the group consisting of acrylic acid, methacrylic acid, an alkyl ester thereof, and substituted or unsubstituted aryl esters are mainly used as acryl based binder resins soluble in the alkaline solution.
- a compound of the above b), as a crosslinking compound having at least two ethylenically unsaturated bonds includes polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1 ,3-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1 ,6-hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, pentaerythritol hexa(meth)acrylate, etc.
- this crosslinking compound is simply distributed in a binder resin of the composition, and when it is exposed to an active light such as ultraviolet rays, etc., a crosslinking reaction occurs and a network structure is formed preventing an alkaline soluble resin from dissolving by a developer in the development process, consequently playing a role in the leaving of images on a substrate.
- crosslinking compounds when crosslinking compounds are excessively used to prevent this phenomena, not only are process properties decreased by surface hardness deterioration after exposure to light, but also process yields decrease as an exposing amount to light causing sufficient crosslinking reaction increases.
- the present invention provides a photosensitive resin composition
- a photosensitive resin composition comprising a self-curable binder resin, a photopolymerization initiator, a crosslinking compound having at least two ethylenically unsaturated bonds, and a solvent
- the self-curable binder resin is the following Chemical Formula 1 : [Chemical Formula 1] - A - B - C - where A is a compound represented as in the following Chemical Formula 1-A; [Chemical Formula 1-A]
- C is a compound represented as in the following Chemical Formula 1-C and / or Chemical Formula 1-C; [Chemical Formula 1-C]
- R 2 is an alkyl group having 1 to 8 carbon atoms, a hydroxy group substituted alkyl group, or a substituted or unsubstituted aryl group having 1 to 12 carbon atoms
- R 3 is a benzene, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a benzene having a C, ⁇ C 6 alkyl substituent, a benzene having a C, ⁇ C 8 alkoxy substituent, or a hydroxide group or a halogen substituted benzene.
- the A portion in the binder resin of Chemical Formula 1 accounts for 10 to 50 mol%, the B portion accounts for 0 to 15 mol%, and the C portion accounts for 50 to 90 mol% of the total binder resin.
- a crosslinking compound having at least two unsaturated groups can further be used in the photosensitive resin composition if necessary.
- a self-curable binder resin of the Chemical Formula 1 is obtained by reacting a copolymer comprising a constituent of a compound having one or more carboxylic acids selected from the group consisting of the following
- R 1 is hydrogen or a methyl group
- R 2 is a compound selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, a hydroxy group substituted alkyl group, and a substituted or unsubstituted aryl group or arylalkyl group having 4 to 12 carbon atoms
- R 3 is a compound selected from the group consisting of a benzene, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a benzene having a C 1 ⁇ C 6 alkyl substituent, a benzene having a C, ⁇ C 8 alkoxy substituent, and a hydroxide group or halogen substituted benzene.
- Formula 4 in a certain mole ratio is put into a flask with a stirrer and a nitrogen injecting hole attached, and then dissolved using a solvent such as methyl ethyl ketone, etc.
- a solvent such as methyl ethyl ketone, etc.
- a self-curable binder resin is prepared by forming precipitates from the reactant using a mixture with a ratio of n-hexane and methanol of 1 :1 , and drying the precipitates under vacuum.
- An epoxy group of a compound of Chemical Formula 5 is reacted with carboxylic acid existing in the binder resin and forming an ester consequently forming a self-curable binder resin, wherein a reactive (meth)acryl group is employed in the linear binder resin as a branch.
- This obtained self-curable binder resin as a resin which is dissolved or at least swelled by an alkaline aqueous solution, can cause the curing reaction by using an active light such as ultraviolet rays, etc.
- the present invention provides a photosensitive resin composition prepared by mixing a copolymer in which a compound of the Chemical Formula 2 is copolymerized with one or both compounds of a compound of the Chemical Formula 3 and a compound of the Chemical Formula 4, a photopolymerization initiator, and a solvent.
- the photosensitive resin composition of the present invention forms a network structure not only with the crosslinking compounds but also with binder resin chains. Because of this, the photosensitive resin composition of the present invention provides the maximized solubility deference between an exposed area and a non exposed. Thus it can be obtained the superior film characteristics as well as the excellent sensitivity and resolution by reducing the amount of crosslinking compound or not using it.
- Acrylic acid, methacrylic acid, etc. can be used as a compound of the Chemical Formula 2, and its consumed amount is from 10 to 90 mol% based on the mole sum of total monomers in the copolymer.
- a compound of the Chemical Formula 3 is preferably a compound selected from the group consisting of benzyl(meth)acrylate, phenyl(meth)acrylate, cyclohexyl(meth)acrylate, methyl(meth)acrylate, ethyl(meth)acrylate, or 2-ethylhexyl(meth)acrylate, and more preferably benzyl(meth)acrylate or phenyl(meth)acrylate.
- a compound of the Chemical Formula 4 is preferably a compound selected from the group consisting of styrene, 4-hydroxystyrene, 4- methylstyrene, or vinyl acetate.
- a compound of the Chemical Formula 5 is preferably glycidyl acrylate or glycidyl methacrylate. This compound uses 0.1 to 90 mol% of the carboxylic acid contained monomer in Chemical Formula 2.
- a crosslinking compound having at least two unsaturated groups which can be used in the present invention if necessary includes a compound selected from the group consisting of polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1 ,3-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1 ,6-hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, trimethylolpropane tri
- the content of the crosslinking compound is from 0 to 200 weight%, and preferably from 0 to 150 weight%, based on the total weight of the self- curable binder resin.
- a photopolymerization initiator example is a compound selected from the group consisting of benzophenones such as benzophenone and acetophenone; substituted benzophenones such as bis-4,4'- dimethylaminobenzophenone and bis-4,4'-diethylaminobenzophenone; triazine based photoinitiators such as 2,4,6-tris(trichloromethyl)-triazine; ketone based photopolymerization initiators such as N-methyl-2-benzoylmethylene- ⁇ - naphthothiazole and 2,2-dimethoxy-1 ,2-diphenylethanon; and a mixture thereof.
- the content of the photopolymerization initiator is preferably from 0.1 to 10 weight% based on the total weight of the photopolymerizable composition.
- a general solvent mainly used in the polymerization of acryl polymer is a compound selected from the group consisting of methylethylketone, cyclohexanone, tetrahydrofurane, methyl cellosolve, methyl cellosolve acetate, dimethyl formamide, propylene glycol methylether acetate, 2-methoxyethylether, and a mixture thereof.
- a pigment small amounts of a pigment, a dyestuff, an antifoaming agent for increasing filming properties, a surfactant, a thermal polymerization preventing agent, an adhesion promoter, etc. in addition to the above basic components can be used in a photosensitive resin composition of the present invention if necessary.
- the finally obtained photosensitive resin composition solution is filtered using a membrane filter having 0.1 to 5 ⁇ m pores.
- This filtered resin composition is filmed using a notified method such as a spin coating method, a roll coating method, a spray coating method, etc.
- a glass plate or a silicone wafer can be used as a filming substrate, wherein the film surface thickness is determined by filming conditions such as composition viscosity, concentration of solid content, filming rate, etc., and a 0.1 to 500 ⁇ m thick thin film can be obtained using a composition of the present invention.
- the obtained thin film is pretreated by maintaining a temperature of 50 to 150 ° C at a heating plate or an oven for 10 to 500 seconds.
- Ultraviolet rays are irradiated on the somewhat dried thin film through a positive type test photomask (made by Toppan Printing Co., Ltd.), wherein the ultraviolet ray light is irradiated in the intensity of illumination of from about 30 to
- the solubility of the ultraviolet ray irradiated area becomes far less than that of the non-ultraviolet ray irradiated area, thus maximizing the solubility difference between them.
- the ultraviolet ray irradiated thin film is developed by a spray method or a dipping method at a temperature of 20 to 30 ° C , wherein a KOH aqueous solution having from 9 to 12 pH or 0.1 to 5 weight% of tetramethylammonium hydride aqueous solution can be used as a developer.
- SYNTHESIZING EXAMPLES and EXAMPLES are described as follows in order to help understand the present invention. However, the following SYNTHESIZING EXAMPLES and EXAMPLES are only for help understand the present invention, and the present invention is not limited to the following SYNTHESIZING EXAMPLES and EXAMPLES. [SYNTHESIZING EXAMPLE 1]
- a binder resin was obtained according to the method of
- a binder resin was obtained according to the method of
- a binder resin was obtained according to the method of SYNTHESISING EXAMPLE 1 except that 10 g of copolymer in which the mole ratio of benzylmethacrylate : methacrylic acid was 70 : 30 and the number average molecular weight was 10,000 were used, and 0.04 g of glycidyl acrylate were also used.
- a binder resin was obtained according to the method of
- a photosensitive resin composition of the present invention was prepared using a binder resin prepared in the above SYNTHSIZING EXAMPLES 1 to 6.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 1. [Table 1]
- the above prepared composition solution was filtered using a Teflon membrane filter having 0.2 ⁇ m pores.
- a photosensitive resin composition was coated on a glass plate using a spin method, put on a heating plate, and maintained at a temperature of 80 ° C for three minutes.
- a positive type test photomask made by Toppan Printing Co., Ltd.
- ultraviolet rays were irradiated thereon, wherein ultraviolet ray light was irradiated at the intensity of illumination of 100 mJ/cm 2 using a 1 kW high pressure mercury lamp containing g, h, and i lines, and particular optical filters were not used.
- the ultraviolet ray irradiated thin film was developed by dipping it into a KOH aqueous solution developer having a pH of 10.5, for two minutes. After washing the thin film coated glass plate with distilled water, it was dried by blowing nitrogen gas and heated in a heating oven at 250 ° C for one hour. The obtained film thickness was 3.5 ⁇ m and clear patterns having 8 ⁇ m of line width and gap could be obtained.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 2.
- a film was formed from the above prepared photosensitive resin composition in a method as in EXAMPLE 1 , exposed at the intensity of illumination of 100 mJ/cm 2 , and developed.
- the obtained film thickness was 3.5 ⁇ m and clear patterns having 7 ⁇ m of line width and gap could be obtained.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 3.
- a film was formed from the above prepared photosensitive resin composition in a method as in EXAMPLE 1 , exposed at the intensity of illumination of 150 mJ/cm 2 , and developed.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 4. [Table 4]
- a film was formed from the above prepared photosensitive resin composition in a method as in EXAMPLE 1 , exposed at the intensity of illumination of 150 mJ/cm 2 , and developed.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 5. [Table 5]
- a film was formed from the above prepared photosensitive resin composition in a method as in EXAMPLE 1 , exposed at the intensity of illumination of 150 mJ/cm 2 , and developed.
- the obtained film thickness was 3.8 ⁇ m and clear patterns having 9 ⁇ m of line width and gap could be obtained.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 6.
- a film was formed from the above prepared photosensitive resin composition in a method as in EXAMPLE 1 , exposed at the intensity of illumination of 100 mJ/cm 2 , and developed.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 7.
- a photosensitive resin composition was prepared not by synthesizing a binder resin first, but by putting the starting material together with constituents comprising the photosensitive resin composition in the present EXAMPLE 7, different from the above EXAMPLES. [Table 7]
- a film was formed from the above prepared photosensitive resin composition in a method as in EXAMPLE 1 , exposed at the intensity of illumination of 150 mJ/cm 2 , and developed.
- the obtained film thickness was 3.6 ⁇ m and clear patterns having 8 ⁇ m of line width and gap could be obtained.
- a photosensitive resin composition was prepared in compositions represented as in the following Table 8. [Table 8]
- the obtained thin film thickness was 3 to 5 ⁇ m and clear patterns having 7 to 9 ⁇ m of line width and gap could be obtained when the exposed light quantity was irradiated at the intensity of illumination of 100 to 150 mJ/cm 2 .
- the present invention can provide a photosensitive resin composition having process benefits, and superior resolving power and film properties since although less exposed light quantity is applied, a photosensitive resin composition using a self-curable binder resin can obtain much clearer and finer patterns compared with existing compositions, thus shortening time of UV exposure process.
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- General Physics & Mathematics (AREA)
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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JP2001517215A JP2003507758A (en) | 1999-08-17 | 2000-08-10 | Photosensitive resin composition |
EP00952027A EP1410108A2 (en) | 1999-08-17 | 2000-08-10 | Photosensitive resin composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR10-1999-0033884A KR100493961B1 (en) | 1999-08-17 | 1999-08-17 | Photosensitive resin composition |
KR1999/33884 | 1999-08-17 |
Publications (2)
Publication Number | Publication Date |
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WO2001013175A2 true WO2001013175A2 (en) | 2001-02-22 |
WO2001013175A3 WO2001013175A3 (en) | 2001-06-14 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/KR2000/000883 WO2001013175A2 (en) | 1999-08-17 | 2000-08-10 | Photosensitive resin composition |
Country Status (5)
Country | Link |
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EP (1) | EP1410108A2 (en) |
JP (1) | JP2003507758A (en) |
KR (1) | KR100493961B1 (en) |
TW (1) | TWI286666B (en) |
WO (1) | WO2001013175A2 (en) |
Cited By (6)
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JP2004206099A (en) * | 2002-12-13 | 2004-07-22 | Dainippon Printing Co Ltd | Photoreactive compound for color splitting light-transmissive structure and color splitting light-transmissive structure |
WO2008097065A1 (en) * | 2007-02-08 | 2008-08-14 | Lg Chem, Ltd. | Alkali-developable resins, method for preparing the same and photosensitive composition comprising the alkali-developable resins |
JP2010044427A (en) * | 2002-12-13 | 2010-02-25 | Dainippon Printing Co Ltd | Photoreactive compound for color splitting light-transmissive structure and color splitting light-transmissive structure |
WO2011138176A1 (en) | 2010-05-03 | 2011-11-10 | Basf Se | Color filter for low temperature applications |
US8119327B2 (en) | 2002-03-28 | 2012-02-21 | Huntsman Advanced Materials Americas Llc | Polymerisable composition |
US8389621B2 (en) | 2007-06-19 | 2013-03-05 | Cheil Industries Inc. | Thermosetting resin composition for producing color filter for CMOS image sensor, color filter comprising transparent film formed using the composition and CMOS image sensor using the color filter |
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KR20050070619A (en) * | 2003-12-30 | 2005-07-07 | 제일모직주식회사 | Photosensitive resin composition for color filter |
JP4571417B2 (en) * | 2004-02-18 | 2010-10-27 | ユニチカ株式会社 | Laminated film with an easy adhesion layer |
KR100709891B1 (en) * | 2004-03-22 | 2007-04-20 | 주식회사 엘지화학 | Alkali-developable resins and photosensitive composition comprising the same |
WO2006080786A1 (en) | 2005-01-25 | 2006-08-03 | Lg Chem. Ltd. | Thermally curable resin composition with extended storage stability and good adhesive property |
KR100835605B1 (en) * | 2007-06-19 | 2008-06-09 | 제일모직주식회사 | Thermosetting resin composition for color filter of cmos image sensor and color filter using the composition, and cmos image sensor using the color filter |
KR20110120124A (en) | 2010-04-28 | 2011-11-03 | 주식회사 엘지화학 | Alkali soluble polymer compounds and photoresist resin composition comprising the same |
KR20140003343A (en) | 2012-06-29 | 2014-01-09 | 주식회사 엘지화학 | Composition for manufacturing resin, resin manufactured by using the same, curable resin composition comprising resin, photosensitive material manufactured by using the photoresist resin composition, and display device comprising the same |
KR101603844B1 (en) | 2013-06-18 | 2016-03-15 | 주식회사 엘지화학 | Curable composition, cured film manufactured by using the curable composition and display device having the same |
KR101603845B1 (en) | 2013-06-18 | 2016-03-15 | 주식회사 엘지화학 | Copolymer, photosensitive resin composition comprising the same, photosensitive material manufactured by using the photosensitive resin composition and display device having the photosensitive material |
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- 2000-08-10 WO PCT/KR2000/000883 patent/WO2001013175A2/en active Application Filing
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Cited By (10)
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US8119327B2 (en) | 2002-03-28 | 2012-02-21 | Huntsman Advanced Materials Americas Llc | Polymerisable composition |
JP2004206099A (en) * | 2002-12-13 | 2004-07-22 | Dainippon Printing Co Ltd | Photoreactive compound for color splitting light-transmissive structure and color splitting light-transmissive structure |
JP2010044427A (en) * | 2002-12-13 | 2010-02-25 | Dainippon Printing Co Ltd | Photoreactive compound for color splitting light-transmissive structure and color splitting light-transmissive structure |
WO2008097065A1 (en) * | 2007-02-08 | 2008-08-14 | Lg Chem, Ltd. | Alkali-developable resins, method for preparing the same and photosensitive composition comprising the alkali-developable resins |
US8304169B2 (en) | 2007-02-08 | 2012-11-06 | Lg Chem, Ltd. | Alkali-developable resins, method for preparing the same and photosensitive composition comprising the alkali-developable resins |
US8389621B2 (en) | 2007-06-19 | 2013-03-05 | Cheil Industries Inc. | Thermosetting resin composition for producing color filter for CMOS image sensor, color filter comprising transparent film formed using the composition and CMOS image sensor using the color filter |
WO2011138176A1 (en) | 2010-05-03 | 2011-11-10 | Basf Se | Color filter for low temperature applications |
WO2011138287A1 (en) | 2010-05-03 | 2011-11-10 | Basf Se | Color filter for low temperature applications |
US9575230B2 (en) | 2010-05-03 | 2017-02-21 | Basf Se | Color filter for low temperature applications |
US10690825B2 (en) | 2010-05-03 | 2020-06-23 | Basf Se | Color filter for low temperature applications |
Also Published As
Publication number | Publication date |
---|---|
TWI286666B (en) | 2007-09-11 |
WO2001013175A3 (en) | 2001-06-14 |
KR20010018075A (en) | 2001-03-05 |
KR100493961B1 (en) | 2005-06-10 |
JP2003507758A (en) | 2003-02-25 |
EP1410108A2 (en) | 2004-04-21 |
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